The Five Worst Sexual Encounters I’ve Ever Had

1. New Year’s Eve 2008 was a rough one for me. I was a year shy from graduating college, not exactly sure what do with my life, and freshly single. Admittedly I was lonely and kind of desperate when I invited over my manager from this bakery I worked at for “drinks and Netflix”, which, in the dating world, means “light chatter before 69’ing.” I really didn’t want to have sex with her. I shouldn’t have invited her over, but I did. She came over and I immediately realized the gravity of the situation. She wanted me and I wanted nothing of it. We walked around the city for hours…hours trying to find things to do. We resorted to getting really drunk and walking up to 53rd and 6th for Halaal. At one point, after she fumbled her hand into mine, I came clean and told her I wasn’t interested in sex. She looked at me and said: “you’re joking, right? You seriously don’t want this?” I told her I didn’t, but she persisted. “You’re fucking kidding. We’re having sex tonight.” I insisted that I really really didn’t want to have sex, but she pushed on. She followed me home and asked if she could sleep over. Being the intoxicated, weak-willed bastard I am, I complied and she got into my bed. I went into the bathroom to brush my teeth and came back to her naked in my bed. “I’m not wearing anything,” she said. I sighed and got under the covers. We had sex. It actually wasn’t that bad, but I was just more upset at my lack of integrity.

2. You know those types of people who immediately tell you they’re amazing at sex? The types who are like: “oh yeah, I like it rough.” Typically, those kind of people are the worse at sex. This girl I had met through a friend and was immediately interested. That is, until she attempted to sextually harass me. She would send me all these texts like “I’ll be the best lay you’ll ever have” and “No one is going to fuck you like me”, to which I immediately became skeptical. Rightfully so, too. The sex was completely sloppy and awkward. It’s like when you take two magnets and point the same sides together. There was no rhythm and I remember kissing her was like trying to stick my tongue in a bathtub. Some people fake orgasms on purpose and some do it out of habit. She moaned during sex as if she was kidnapped by a group of female pornstars at a young age and coached on how to make the fakest sex sounds possible. She shrieked, called me daddy, and probably woke up her entire fucking neighborhood with her booming yells of faux-pleasure. My penis shriveled from our lack of chemistry and I through in the towel early. “I’m pushin’ rope,” I told her as I laid down defeated and supremely grossed out. Then, she asked me in this tiny schoolgirl voice: “Um, I have a teensy little question.” I sighed, knowing exactly what she was going to say. “But um…can I suck your dick?” I sighed again, her question and tone reminiscent of a big budget 90’s action film. We all know how this is going to end. “Sure,” I said, “Go for it.” She did. It was fine.

3. I don’t remember much about this girl. She was my waitress at some restaurant and I jokingly left her my business card, not thinking she’d actually text me. She did one night at 2:00 in the morning. “What are you up to?” any time after midnight equates to “come over and have sex with me.” So I biked over and we watched True Grit together. I think she had a pet snake, which I couldn’t stop staring at during the sex. She kept asking me if I was wearing a condom, to which I kept telling her yes. Regardless of the fact that she could have simply looked down at any point and seen the condom on me, she didn’t believe I had one on. Things got really weird when I stopped halfway through to ask her questions about her pet snake. She went into the bathroom for a long time, which I took as a cue to leave. She came out naked and I was tying my shoes and she asked me one more time if I had been wearing a condom during the sex. I went home, realized I left my glasses at her place and fell asleep unfulfilled in so many ways. The next day I got my glasses, gave her an excruciatingly uncomfortable kiss on the cheek and went home. Weeks later she texted me in the middle of the night “I think I’m pregnant.” To turn a long story short. She wasn’t…because I wore a condom.

4. I met this girl on the Internet during the time where I’d fuck a mailbox if it had a soft enough interior slot. She was easily the most unpleasant person I’d ever met and gave even less of a fuck about life than I did at the time. Her diet consisted of McDonald’s and vodka every day and her hygiene pretty much reflected that choice. Almost out of necessity (being we had both just gotten out of long relationships) we kept seeing each other. She was rude, abrasive, and irritating. I was in her bed one night sipping her favorite drink, vodka and milk, when she stands up, takes off her pants, and says: “are we going to fuck or what?” She was boney and skinny and it felt like I was fucking a telephone pole. The next morning I woke up hungover and sore and she asked me what happened last night. I laughed and shrugged it off until she asked me again, insisting that she had no idea what happened. I was grossed out.

5. Some sexual encounters are bad and some shred your self-confidence to the core. This girl achieved both. I had just moved to New York and was interviewing people to be my roommate. She came in and I found her attractive. Right off the bat I noticed she had the classic crazy-eyes all men warn you about. They were distant, vacant, and wide. I knew I’d never live with her, so I figured I’d give sex a whirl. We met at her laundromat where she pointed out how funny it was that I was watching her fold her underwear. “That’s the only time you’ll see them,” she joked, unable to recognize saying something like that means the direct opposite. We went to a bar where I drank way too much beer and we stumbled back to her place. Let’s backtrack: this wasn’t her place. She was dog-sitting for a friend. Let’s backtrack more: she was caring for two dogs, both of which were staying with her in her closet-sized room. So we get back to her room and it smells like puppy-shit. We sit on her bed and my eyes are watering from all the collected animal dander. We start going at it until all the external elements + my heavy intake of beer nukes my penis. I mumble sorry and tell her I’ve had too much to drink. Ladies, sometimes alcohol kills erections. It’s not our fault, it just happens. She didn’t know that. She looked at me and said: “How?!” I’ll never forget that “how”. So angry, so completely devoid of understand. We tried to have sex again, but the added pressure and particles of dog in the air killed it faster than the first time. She said “Ugh, you’re fucking joking,” and rolled off. Confidence shattered, I turned over and fell asleep. Oh, and then she made fun of my tattoo. Oh, also I got scabies from sleeping in her bed.